Diamond Head Oahu

Oahu Vacation Packages

 
Oahu, "The Gathering Place," is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cuisine. The North Shore is a surfer's paradise, home to the Banzai pipeline and scenic rainforests, offering a laid-back island style visitors are sure to enjoy. To the West, Pearl Harbor is rich in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture give Oahu a flavor all its own. Enjoy the best deals to Oahu with our Hawaii vacation packages.

Endless Summer in Hawaii
$100 OFF per booking

Room upgrades, resort credits, FREE breakfast offers, and more
  • Book by 11/02/25 for select travel through 06/30/26
  • Hilton Hawaiian Village Waikiki Beach Resort
    Hilton Hawaiian Village Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Lush grounds, six spectacular pools, a beachfront lagoon, waterfalls and an array of shops and restaurants are all part of the "Village" experience at this expansive resort.

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  • OUTRIGGER Waikiki Beach Resort
    OUTRIGGER Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Escape to sun, sand & surf on legendary Waikiki Beach. From the beach boys to Duke's Waikiki, experience beach life with live music and entertainment, vibrant cultural events, and accommodations overlooking iconic Waikiki Beach and Diamond Head.

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  • 'Alohilani Resort Waikiki Beach
    'Alohilani Resort Waikiki Beach
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This family-friendly resort across from Waikiki Beach is within easy walking distance of shops, restaurants, and attractions.

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  • The Twin Fin
    The Twin Fin
    Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    Affording stunning views of iconic Diamond Head and steps from Waikiki Beach, this lively hotel with an urban-Hawaii vibe invites guests to embrace the Aloha Spirit with daily activities, regional cuisine and live entertainment.

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  • Sheraton Waikiki Beach Resort
    Sheraton Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Vivid by day, vibrant by night this exceptional oceanfront resort features newly renovated rooms and suites with spectacular ocean views, award-winning outdoor pools, and Waikiki's best family-friendly location.

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  • OUTRIGGER Reef Waikiki Beach Resort
    OUTRIGGER Reef Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This distinctive, refined hotel presents a new vision of hospitality, combining timeless traditions with modern elegance.

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  • Waikiki Beach Marriott Resort & Spa
    Waikiki Beach Marriott Resort & Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Treat yourself to a luxury escape in Honolulu at this beachfront hotel with unparalleled service, thoughtful amenities and sweeping views of the Pacific Ocean.

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  • The Ambassador Hotel of Waikiki, Tapestry Collection by Hilton
    The Ambassador Hotel of Waikiki, Tapestry Collection by Hilton
    Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    At the gateway to Waikiki, this hotel connects guests with the creative and modern spirit of the neighborhoods of Honolulu. Centered around Waikiki’s creative culture, it’s a neighborhood hotel made for more than beach days.

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  • Waikiki Malia
    Waikiki Malia
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Located in central Waikiki within walking distance of luxury shopping and many dining options, this hotel offers spacious guest rooms with tasteful accents and refined decor for an intimate, energizing, and rejuvenating getaway.

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  • Aston Waikiki Sunset
    Aston Waikiki Sunset
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    This Waikiki haven has an easy-going island vibe and awe-inspiring views of iconic Diamond Head.

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Hawaii $100 OFF per booking Offer: Valid on new bookings made 08/25/2025 – 11/02/2025 for select travel 08/25/2025 – 06/30/2026 unless otherwise stated. Minimum 5-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]